How to Get Through Founder's Despair

Chris Heivly co-founded MapQuest (which sold to AOL for $1.2 billion), was sole managing director of 77 Capital (a $25 million venture fund), and has been an executive at five software companies. Currently, he is one of two managing directors of The Startup Factory, a seed investment fund making 10 to 14 new investments per year. A national writer and speaker about startups and startup communities, Heivly is also the founder of the Big Top Job Fair.

This start-up stuff is really hard, right? Are you starting to wonder whether yours will work? Is doubt creeping in? Are the conversations between you and your cofounder(s) moving from spirited to…weary? Do you find yourself just a little less focused than you were a few months ago?

You are in the valley.

Those of us with multiple rodeos under our belts know that the valleys are inevitable. If this is your first start-up, however, the valleys will kick your ass. Did you really think you were going to be the exception? Did you think your start-up would take off and your biggest challenge would be managing exponential growth?

You probably did. That’s how entrepreneurs are made.

Managing the valley is the hard part of the first months, or the first year, of a start-up’s life. You’ll have to cross the valley if you’re going to have a company.

Here, from someone who has been there, are a couple of tools to help you.

First, recognize what’s happening, because that’s how you control it. Listen to yourself. Literally: is your voice getting louder or more intense? Are you sleeping more or sleeping less than normal? Have you significantly altered your normal routines, such as eating more or discontinuing your workout? Negative changes to your routine are a clear signal that something is amiss.

Look yourself in the mirror and be prepared to see what you probably already know.

Second, trust someone. Find a safe peer or mentor who will laugh, cry, listen, and empathize. This is not a strategic business adviser or one of your investors. It certainly is not one of your employees or co-founders, regardless how close the two of you might be. This is someone who has lived this before. Find him or her. Invite him or her to drink coffee or a beer, and always meet outside of your office space. This person’s role is to empathize and not to advise per se.

If you can’t recognize and prepare for the valleys, your company won’t make it. You will inevitably decide to shut it down, because you cannot see anything but the valley. It might be the right decision, but your emotional baggage and lack of valley experience is preventing the clearest decision.